tert-Butyl ((S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethyl)carbamate → (2R,3S)-1-((1S,3R)-3-(allyloxy)-6-propoxy-2,3-dihydro-1H-inden-1-ylamino)-3-amino-4-(3,5-difluorophenyl)butan-2-ol

Participants

Reaction Steps

Step BA (1): (1S,3R)-3-(allyloxy)-6-propoxy-2,3-dihydro-1H-inden-1-amine (940 mg, 3.8 mmol, from Step AY (1)) was reacted with tert-butyl (S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethylcarbamate (1.0 g, 3.3 mmol) following a procedure analogous to Step AW (1) to afford, after purification, 1.2 g (66% yield) of (2R,3S)-1-((1S,3R)-3-(allyloxy)-6-propoxy-2,3-dihydro-1H-inden-1-ylamino)-3-amino-4-(3,5-difluorophenyl)butan-2-ol. LC-MS (M+H)+=547.20. 1H NMR (300 MHz, CDCl3) δ 0.9-1.1 (t, 3H) 1.3 (s, 9H) 1.7-1.9 (m, 2H) 1.9-2.0 (m, 1H) 2.5-3.1 (M, 5H) 3.4-3.5 (m, 1H) 3.7-3.8 (m, 1H) 3.8-4.0 (t, 2H) 4.0-4.1 (m, 2H) 4.5-4.6 (m 1H) 4.7-4.8 (m, 1H) 5.1-5.4 (m, 2H) 5.8-6.0 (m, 1H) 6.5-6.9 (m, 5H) 7.2-7.3 (d, 1H).

Provenance & Evidence